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A comprehensive study on crystal structure of a novel sulfonamide-dihydroquinolinone through experimental and theoretical approaches

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Abstract

Quinolinones and sulfonamides are moieties with biological potential that can be linked to form new hybrid compounds with improved potential. However, there are few hybrids of these molecules reported. In this sense, this work presents a structural description of a new sulfonamide-dihydroquinolinone (E)-2-(2-methoxyphenyl)-3-(3-nitrobenzylidene)-1-(phenylsulfonyl)-2,3 dihydroquinolin-4(1H)-one (DHQ). The molecular structure of DHQ was elucidated by X-ray diffraction, nuclear magnetic resonance and infrared spectroscopy, and both molecular packing and intermolecular interactions were analyzed by Hirshfeld surfaces and fingerprint maps. In addition, theoretical calculations on frontier orbitals, molecular electrostatic potential maps, and assignments were performed. The crystal packing of DHQ was found to be stabilized by a dimer through a weak C–H⋯O interaction along the c axis. Moreover, the structure is stabilized mainly by C–H⋯O and C–H⋯π interactions, since the interaction C25–H25⋯π contributes to a chain formation. The Hirshfeld normalized surface shows that the closest interactions are around the atoms linked to the dimer formation. The calculations indicate that DHQ possesses electrophilic sites near O atoms and depleted electrons around the H atoms. There is a band GAP of 3.29 eV between its frontier orbitals, which indicates that DHQ is more reactive than other analogues published.

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Acknowledgments

The authors would like to thank the financial support of Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES). This research was developed with support of the High Performance Computing Center of Universidade Estadual de Goiás (UEG).

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Authors and Affiliations

  1. Grupo de Química Teórica e Estrutural de Anápolis, Universidade Estadual de Goiás, Anápolis, GO, Brazil

    C. A. Moreira, W. F. Vaz & H. B. Napolitano

  2. Instituto de Química, Universidade Federal de Goiás, Goiânia, GO, Brazil

    J. M. F. Custódio, G. D. C. D’Oliveira & C. Noda Perez

  3. Laboratorio de Novos Materiais, Centro Universitário de Anápolis, Anápolis, GO, Brazil

    H. B. Napolitano

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  1. C. A. Moreira
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Correspondence to J. M. F. Custódio.

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Moreira, C.A., Custódio, J.M.F., Vaz, W.F. et al. A comprehensive study on crystal structure of a novel sulfonamide-dihydroquinolinone through experimental and theoretical approaches. J Mol Model 25, 205 (2019). https://doi.org/10.1007/s00894-019-4091-7

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